Methanol → HCID 58914741, compound

HRID 1297770Notes

Reaction equation

HRID 1297770 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:38]=[CH:37][CH:36]=[CH:35][C:5]=1[CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:25]2[CH:30]=[C:29]([CH3:31])[C:28]([OH:32])=[C:27]([CH3:33])[CH:26]=2)([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=2)[C:8]1=[O:34].[CH3:39]O>C1COCC1>[NH2:22][C:19]1[CH:18]=[CH:17][C:16]([C:9]2([C:25]3[CH:30]=[C:29]([CH3:31])[C:28]([O:32][CH3:39])=[C:27]([CH3:33])[CH:26]=3)[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[N:7]([CH2:6][C:5]3[CH:35]=[CH:36][CH:37]=[CH:38][C:4]=3[Cl:3])[C:8]2=[O:34])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydride2×HCID 58914687HCID 58914687, compound

Product 1

HCID 58914741HCID 58914741, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve nickelous chloride (36 mg, 0.15 mmol) in methanol (3 mL). Add sodium borohydride (17 mg) followed 1-(2-chloro-benzyl)-3-(4-hydroxy-3,5-dimethyl-phenyl)-3-(4-nitro-phenyl)-1,3-dihydro-indol-2-one (152 mg, 0.3 mmol) in THF (3 mL). Add additional sodium borohydride and stir at room temperature for 30 min. Concentrate to dryness and partition the resulting residue in water/ethyl acetate. Separate and extract aqueous with ethyl acetate (2×). Wash combined organic portions with brine and then dry (MgSO4), filter and concentrate in vacuo to give 145 mg of residue. Purify by flash chromatography (gradient of 10% EtOAc/hexanes to 50% EtOAc/hexanes) to give 97 mg (67%) of the title compound as a white foam. MS (ES): m/z=483 (M+1); 1H NMR(DMSO-d6): δ9.99 (s, 1H), 7.53 (m, 3H), 7.36-7.24 (m, 4H), 7.10 (t, J=8 Hz, 1H), 6.95 (m, 2H), 6.85 (m, 4H), 6.52 (d, J=8.5 Hz), 5.19 (bs, 2H), 5.06 (s, 2H) 3.65 (s, 3H), 2.16 (s, 6H).

Workup

  1. concentrationConcentrate to dryness
  2. custompartition the resulting residue in water/ethyl acetate
  3. customSeparate
  4. extractionextract aqueous with ethyl acetate (2×)
  5. washWash
  6. dry with materialdry (MgSO4)
  7. filtrationfilter
  8. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-c29f897e6a6c48dcb86b33d91fc278e3
Source dataset
uspto-grants-2007_07
Patent number
US07250442B2

Reaction notes

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